The Biggest Mistake I Ever Made

Jason Warner
7 min readJan 31, 2016

There was a time in my life when I played quite a bit of basketball. I was leading engineering at a start-up in Scottsdale, AZ, my wife was doing her residency, and we didn’t have kids yet. Other than work, I had plenty of time and I filled it with basketball. I would typically play three to four mornings, in one or two leagues in the evenings, and do shooting drills for fun on the weekends.

I started a team in one of those leagues and recruited a few players I knew to play. None of us were unusually skilled, just a few working professionals who happened to like basketball and got along amazingly well. As is typical with new teams, we weren’t very good in the beginning. We were all decent players in our own right, but we didn’t gel as a team yet and it showed in the early games. By the end of the first season there were glimpses of what we could be, though we didn’t make the playoffs. By the end of the second season, when we lost in the championship game, we knew we were good. The third season we dominated the league. This continued for a few more seasons. We had a core group of about five players and a few other players rotated in and out. It helped that we had a base skill level, but our real strength was our game plan: play fast, shoot if you are open, pass if you aren’t, trust each other, have fun, it’s only basketball.

One season a new player asked to join the team. He was a semi-pro player, easily the best player in the league, and he was between his seasons in Europe and Mexico. The team talked it over and we said “sure”. He seemed like a nice enough guy, he certainly had the skill and we could always use another great player (the league was getting tougher and tougher as the seasons went on).

At this point we had won maybe four or five straight championships. We expected to repeat again. Our first few games were rough, but we managed through them. We weren’t quite ourselves though we thought it was just about integrating this new player into our flow and style and adapting to his. He certainly showed his skills. In a few of those games he scored over 50 points, once topping 60. He was a monster. He could do whatever he wanted on the court, go anywhere. No one could stop him.

The cracks started around the fifth or sixth game, our second straight loss where he scored a ton of points, dominated the ball and started yelling at teammates. After our third straight loss, the wheels fell off our season and we didn’t make the playoffs.

It was clear he and the team weren’t mixing, but what was also clear was how good a player he was. He certainly was the best player in the league by a wide margin. I asked the team if we wanted him to come back for another season to try and make it work, this time adapting more to his style than asking him to adapt to ours. The team agreed. There was no denying how good he was. I talked to him, told him we were disappointed by the season, wanted him to come back, how the team was going to work around his style more. I also had a very frank, very real conversation about being a better teammate. He said the right things, though I was skeptical.

I asked him to leave the team after our fourth game the following season. I didn’t ask the team, I just made the decision. He wasn’t welcome on any team I was captain of and I owed it to the other guys to do something about it. We were 1–3, in last place and it was clear the team was fraying. We’d been together for a few years at this point and it was going downhill fast. Very fast.

We ended the season needing a win to make it into the playoffs, which we won, making a run in the playoffs, culminating in a loss in the championship game. I have never seen a team so, not happy, but relieved, to lose a championship game. We were back, the team was back and more importantly, we had each other’s backs. We lost, but it felt right again.

It was this experience that made me realize I was in the middle of making the biggest mistake of my young management career right around the same time. It still remains my biggest mistake, and the one I regret the most to this day. I held back my teams, the company and our products by not making a tough decision and letting someone go at work.

This person was an exceptionally sharp programmer. Everyone on the teams looked up to him. He had been with the company since the early days and not only knew our systems, but he seemed like a wizard in his depth of general computing knowledge. Everyone was in awe of his abilities.

He was also an incredibly frustrating person to deal with, was hard to work with, never seemed to completely finish something or follow-through, had a very pessimistic outlook on almost everything, and was an incredible time sink for myself and another senior leader in the company. Even so, everyone generally put up with him for the perceived benefits of his knowledge and productivity.

But, I decided, it was time. He had to adapt more to us or I had to let him go. I started the process with more intensive coaching, giving him one last chance with incredibly clear expectations and criteria. It didn’t work. I began the exit process and was blocked by the founder. The founder thought he was too valuable to let go and stopped me from moving forward. I pushed, the founder pushed back again, and I didn’t push more (another mistake).

The founder took him out of engineering and used him in a different role away from the engineering teams. The teams themselves wondered how they would manage without him, but they never missed a beat. Instead, new leaders emerged and in a few short weeks it was business as usual. In a few months the teams were more productive than ever and in less than half a year morale was the highest it had ever been.

Fast forward a year or so, I’ve physically moved continents to Australia and am no longer with the company. I get word from my friends that the founder finally pulled the trigger and let this person go. It didn’t work with the founder either.

The founder and I made the most classic of mistakes: putting up with someone because we were afraid to lose their ability. I’ve since come to learn over and over again, it’s almost never worth it.

Life is full of lessons, some learned the hard way and some the easy way. I consider this lesson learned the hard way. I’m happy I learned it, though, and I’m glad I can share it. Practically speaking, there is depth to the experience that might have been missed if you hadn’t experienced it.

First and foremost, have the fortitude to let the most talented or skilled person who also happens to be an asshole leave the company. Coach them out, ask them to leave, let them go if they decide to. You, as a leader, owe it to everyone else to make a tough call and make everyone else’s lives better.

Second, solicit feedback from the team, but don’t ask them to make a call on it. You, as the leader, make the call. People, by nature, want to give people a second, third, ninth chance. They don’t want to see something unfortunate happen to someone. And they certainly don’t want to be the cause of it. Don’t put them in that situation. You are responsible, you do it. Show them how to do it, coach them on how to do it, but don’t ask them to make the call or to do it.

Finally, guard your team from risk both externally and internally. And don’t assume you’ll see the risk coming. This team member had been a long time employee of the company. The company had put up with him for quite some time, too long in fact. However, there was a point in the company’s growth where it was clear he and the company were no longer a fit. This happens. It’s extremely unfortunate. I hate these situations and I over-coach people in these situations more than I do in others because of how unfortunate I feel about it. It shouldn’t, however, change the outcome if the same outcome is needed. Make the call.

I have since seen and coached others through this multiple times. I have the benefit of experience though I know this can be one of the scariest situations for less experienced leaders to see. You never want to lose someone you view as as a supreme technical talent, let alone a long time employee of a company. The most practical way of looking at it is that you are actually holding back everyone else at the expense of this person. Don’t do that. You also have a responsibility to those folks and need to do the collective right thing for your situation. You are also likely holding this person back as well! It’s clear the current situation wasn’t working, a change, even if they know it or not, could be just what they need.

Trust yourself, trust your team, have the hard conversations and make the tough call. Leadership in a nutshell.



Jason Warner

CTO @ GitHub. Previously VP/Head of Engineering @ Heroku, Desktop Engineering @ Canonical/Ubuntu.